(1R,2S,5E,9E)-5,9,13-trimethyl-2-(propan-2-yl)-15-thiabicyclo[9.3.1]pentadeca-5,9,11,13-tetraene

ID: ALA3037799

PubChem CID: 71727208

Max Phase: Preclinical

Molecular Formula: C20H30S

Molecular Weight: 302.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C[C@@H]2SC(=C1)/C=C(\C)CC/C=C(\C)CC[C@H]2C(C)C

Standard InChI:  InChI=1S/C20H30S/c1-14(2)19-10-9-15(3)7-6-8-16(4)11-18-12-17(5)13-20(19)21-18/h7,11-14,19-20H,6,8-10H2,1-5H3/b15-7+,16-11+/t19-,20-/m0/s1

Standard InChI Key:  CDCCHUJOQQLBNW-YVORUKNWSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   13.7368  -11.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4216   -9.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4240  -10.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0964   -9.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4113   -9.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1768  -10.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5950  -11.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2489   -9.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4876  -12.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8871   -9.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7700  -11.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6548  -11.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3809  -11.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4152  -11.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0010  -10.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7411   -9.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8032  -12.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5300  -11.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5798  -10.4873    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.9237  -10.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4624   -8.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 16  1  0
 10 19  1  6
 13 12  1  0
 15  5  1  0
 15 14  1  0
 12 18  1  0
  6 15  1  6
 20  7  1  0
 16  2  2  0
  4  8  2  0
  3 12  2  0
 10  4  1  0
  6  1  1  0
  9 13  1  0
  6 10  1  0
  7 11  2  0
 11  9  1  0
  1 20  1  0
  2  3  1  0
  7 17  1  0
  2 19  1  0
  8 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3037799

   (2E,6E,10S,11R)-3,7,13-trimethyl-10-propan-2-yl-15-thiabicyclo[9.3.1]pentadeca-1(14),2,6,12-tetraene

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 302.53

Molecular Weight (Monoisotopic): 302.2068

AlogP: 6.67

#Rotatable Bonds: 1

Polar Surface Area: 0.00

Molecular Species: ┄

HBA: 1

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.91

CX LogD: 5.91

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.49

Np Likeness Score: 1.76

References

1. Eterović VA, Del Valle-Rodriguez A, Pérez D, Carrasco M, Khanfar MA, El Sayed KA, Ferchmin PA..  (2013)  Protective activity of (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol analogues against diisopropylfluorophosphate neurotoxicity: preliminary structure-activity relationship and pharmacophore modeling.,  21  (15): [PMID:23769165] [10.1016/j.bmc.2013.05.018]

Source

Source(1):

• Scientific Literature